5,5a-dihydrobenzo[ghi]fluoranthene | 255871-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5,5a-dihydrobenzo[ghi]fluoranthene
• 英文别名: Pentacyclo[8.8.0.02,7.03,17.013,18]octadeca-1(10),2(7),3,5,8,11,13(18),14-octaene
• CAS: 255871-46-6
• 化学式: C₁₈H₁₂
• 分子量: 228.293
• InChiKey: RJYISSKJMXJKAL-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  423.2±30.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,5a-dihydrobenzo[ghi]fluoranthene 在 potassium dichromate 、 sodium tetrahydroborate 、 硫酸 、 碘 、 氧气 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 苯 为溶剂， 反应 32.17h， 生成 trans-3,4-dihydroxy-3,4-dihydrobenzo[ghi]fluoranthene
  参考文献：
  名称：

  Synthesis of anti- and syn-Diol Epoxides of trans-3,4-Dihydroxy-3,4-dihydrobenzo[ghi]fluoranthene: Model Planar Diol Epoxides

  摘要：

  We describe the preparation of anti- and syn-3,4-dihydroxy-5,5a-epoxy-3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene (2 and 3) as model planar diol epoxides. These compounds were synthesized by a dihydroarene method in 10 steps starting from 4H-cyclopenta[def]phenanthrene. These are the first examples of diol epoxides in which a five-membered ring is fused to the saturated ring bearing an epoxide group, and they are the rigid analogues of the extensively studied benzo[c]phenanthrene diol epoxides (5 and 6). In accord with expectation, (1)H NMR data indicated that the diol conformations of 2 and 3 are locked into diequatorial and diaxial conformations, respectively, and thus are suitable for comparative DNA binding studies.

  DOI：

  10.1021/jo9907944
• 作为产物：
  描述：

  4-(2'-carboxyethyl)-4H-cyclopenta[def]phenanthrene 在 sodium tetrahydroborate 、 氢氟酸 、 对甲苯磺酸 作用下， 以 乙醇 、 苯 为溶剂， 反应 7.0h， 生成 5,5a-dihydrobenzo[ghi]fluoranthene
  参考文献：
  名称：

  Synthesis of anti- and syn-Diol Epoxides of trans-3,4-Dihydroxy-3,4-dihydrobenzo[ghi]fluoranthene: Model Planar Diol Epoxides

  摘要：

  We describe the preparation of anti- and syn-3,4-dihydroxy-5,5a-epoxy-3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene (2 and 3) as model planar diol epoxides. These compounds were synthesized by a dihydroarene method in 10 steps starting from 4H-cyclopenta[def]phenanthrene. These are the first examples of diol epoxides in which a five-membered ring is fused to the saturated ring bearing an epoxide group, and they are the rigid analogues of the extensively studied benzo[c]phenanthrene diol epoxides (5 and 6). In accord with expectation, (1)H NMR data indicated that the diol conformations of 2 and 3 are locked into diequatorial and diaxial conformations, respectively, and thus are suitable for comparative DNA binding studies.

  DOI：

  10.1021/jo9907944

文献信息

• Synthesis of <i>a</i><i>nti</i>- and <i>s</i><i>yn</i>-Diol Epoxides of <i>trans</i>-3,4-Dihydroxy-3,4-dihydrobenzo[<i>g</i><i>hi</i>]fluoranthene: Model Planar Diol Epoxides
  作者：Hui-Fang Chang、Bongsup P. Cho

  DOI：10.1021/jo9907944

  日期：1999.12.1

  We describe the preparation of anti- and syn-3,4-dihydroxy-5,5a-epoxy-3,4,5,5a-tetrahydrobenzo[ghi]fluoranthene (2 and 3) as model planar diol epoxides. These compounds were synthesized by a dihydroarene method in 10 steps starting from 4H-cyclopenta[def]phenanthrene. These are the first examples of diol epoxides in which a five-membered ring is fused to the saturated ring bearing an epoxide group, and they are the rigid analogues of the extensively studied benzo[c]phenanthrene diol epoxides (5 and 6). In accord with expectation, (1)H NMR data indicated that the diol conformations of 2 and 3 are locked into diequatorial and diaxial conformations, respectively, and thus are suitable for comparative DNA binding studies.